NZ207057A - Substituted amide derivatives and pharmaceutical compositions - Google Patents
Substituted amide derivatives and pharmaceutical compositionsInfo
- Publication number
- NZ207057A NZ207057A NZ207057A NZ20705784A NZ207057A NZ 207057 A NZ207057 A NZ 207057A NZ 207057 A NZ207057 A NZ 207057A NZ 20705784 A NZ20705784 A NZ 20705784A NZ 207057 A NZ207057 A NZ 207057A
- Authority
- NZ
- New Zealand
- Prior art keywords
- ethanethioate
- oxo
- compound
- composition according
- thiazolyl
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- -1 m-trifluoromethylphenyl Chemical group 0.000 claims abstract description 13
- 241001465754 Metazoa Species 0.000 claims abstract description 10
- 208000002193 Pain Diseases 0.000 claims abstract description 9
- 230000036407 pain Effects 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- 230000000202 analgesic effect Effects 0.000 claims abstract description 5
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims description 33
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 235000019359 magnesium stearate Nutrition 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 229910052623 talc Inorganic materials 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- PRMJASBUKNCAPI-UHFFFAOYSA-N n-(4-chlorophenyl)-2-sulfanylacetamide Chemical compound SCC(=O)NC1=CC=C(Cl)C=C1 PRMJASBUKNCAPI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- FMIXVMBNZULERC-UHFFFAOYSA-N 2-sulfanyl-n-(1,3-thiazol-2-yl)acetamide Chemical compound SCC(=O)NC1=NC=CS1 FMIXVMBNZULERC-UHFFFAOYSA-N 0.000 claims description 2
- 208000008035 Back Pain Diseases 0.000 claims description 2
- 229920000084 Gum arabic Polymers 0.000 claims description 2
- 208000007514 Herpes zoster Diseases 0.000 claims description 2
- 208000008930 Low Back Pain Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000025747 Rheumatic disease Diseases 0.000 claims description 2
- 235000010489 acacia gum Nutrition 0.000 claims description 2
- 239000000205 acacia gum Substances 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 230000003387 muscular Effects 0.000 claims description 2
- YSPHRFZMBKXSAX-UHFFFAOYSA-N n-phenyl-3-sulfanylpropanamide Chemical compound SCCC(=O)NC1=CC=CC=C1 YSPHRFZMBKXSAX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000000552 rheumatic effect Effects 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241000978776 Senegalia senegal Species 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000007891 compressed tablet Substances 0.000 claims 1
- 239000007903 gelatin capsule Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- UHHXIXSKZJOLQJ-UHFFFAOYSA-N n-(4-chlorophenyl)-3-sulfanylpropanamide Chemical compound SCCC(=O)NC1=CC=C(Cl)C=C1 UHHXIXSKZJOLQJ-UHFFFAOYSA-N 0.000 claims 1
- DLVKRCGYGJZXFK-UHFFFAOYSA-N n-phenyl-2-sulfanylacetamide Chemical compound SCC(=O)NC1=CC=CC=C1 DLVKRCGYGJZXFK-UHFFFAOYSA-N 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- XCPPBDAMXRLGKI-UHFFFAOYSA-N s-(2-anilino-2-oxoethyl) ethanethioate Chemical compound CC(=O)SCC(=O)NC1=CC=CC=C1 XCPPBDAMXRLGKI-UHFFFAOYSA-N 0.000 claims 1
- HWPBFERTISIUPJ-UHFFFAOYSA-N s-[2-oxo-2-(1,3-thiazol-2-ylamino)ethyl] ethanethioate Chemical compound CC(=O)SCC(=O)NC1=NC=CS1 HWPBFERTISIUPJ-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 102000003729 Neprilysin Human genes 0.000 abstract 3
- 108090000028 Neprilysin Proteins 0.000 abstract 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- 239000003937 drug carrier Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- QPLPMPAMOJIAMN-UHFFFAOYSA-N 3-oxobutanethioic s-acid Chemical compound CC(=O)CC(O)=S QPLPMPAMOJIAMN-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 208000000114 Pain Threshold Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- 231100000021 irritant Toxicity 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 210000001577 neostriatum Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000037040 pain threshold Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- ISJBQSJDQZLCSF-UHFFFAOYSA-N (4-chlorophenyl)azanium;chloride Chemical compound [Cl-].[NH3+]C1=CC=C(Cl)C=C1 ISJBQSJDQZLCSF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 241001591881 Cropia europs Species 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- HIINQLBHPIQYHN-JTQLQIEISA-N Tyr-Gly-Gly Chemical compound OC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1 HIINQLBHPIQYHN-JTQLQIEISA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 108010083141 dipeptidyl carboxypeptidase Proteins 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- XEYWOETXQNDSED-UHFFFAOYSA-N s-(3-chloro-3-oxopropyl) ethanethioate Chemical compound CC(=O)SCCC(Cl)=O XEYWOETXQNDSED-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 108010017949 tyrosyl-glycyl-glycine Proteins 0.000 description 1
- 230000001755 vocal effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicinal Preparation (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8301863A FR2540498B1 (fr) | 1983-02-07 | 1983-02-07 | Nouveaux medicaments derives d'amides d'acide mercaptoacetique et de l'acide 3-mercaptopropionique et les compositions pharmaceutiques les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ207057A true NZ207057A (en) | 1987-07-31 |
Family
ID=9285652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ207057A NZ207057A (en) | 1983-02-07 | 1984-02-07 | Substituted amide derivatives and pharmaceutical compositions |
Country Status (16)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4611002A (en) * | 1977-07-14 | 1986-09-09 | E. R. Squibb And Sons, Inc. | Carboxymethyl esters of mercaptopropanoic acids as enkephalinase inhibitors |
| FR2540495B1 (fr) * | 1983-02-07 | 1986-02-14 | Roussel Uclaf | Nouveaux derives de o-mercaptopropanamide et de ses homologues, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
| US4868310A (en) * | 1986-08-04 | 1989-09-19 | Rohm And Haas Company | Process for preparing isothiazolones |
| DE3639322A1 (de) * | 1986-11-17 | 1988-05-26 | Henkel Kgaa | Verfahren zur reinigung und desinfektion von endoskopen und mittel zur durchfuehrung des verfahrens |
| CA2698928A1 (en) * | 2007-09-28 | 2009-04-09 | Absolute Science, Inc. | Compounds and methods for treating zinc matrix metalloprotease dependent diseases |
| EP2337778A4 (en) * | 2008-09-19 | 2012-05-09 | Absolute Science Inc | METHODS OF TREATING BOTULINUM TOXIN-RELATED DISEASE IN A SUBJECT |
| JP5546947B2 (ja) * | 2010-05-13 | 2014-07-09 | 高砂香料工業株式会社 | 含硫カルボン酸エステル類の製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2709706A (en) * | 1950-05-06 | 1955-05-31 | Goodrich Co B F | Preparation of beta-dithiocarbamyl and beta-mercapto carboxylic acid amides and the corresponding hydrazides |
| FR1193289A (fr) * | 1958-03-14 | 1959-11-02 | Oreal | Procédé pour la mise en plis permanentée de cheveux au moyen de nouveaux composés tensio-actifs et procédé pour préparer ces composés |
| US3770824A (en) * | 1971-05-03 | 1973-11-06 | Monsanto Co | Substituted alpha,alpha-dichloromethane-sulfenyl chlorides and their manufacture |
| US3878248A (en) * | 1971-05-03 | 1975-04-15 | Monsanto Co | Substituted alpha, alpha-dichloro-methane-sulfenyl chlorides |
| AU4091178A (en) * | 1977-10-25 | 1980-04-24 | Merck & Co Inc | Substituted mercapto acid amides |
| US4329495A (en) * | 1981-05-18 | 1982-05-11 | Pfizer Inc. | Enkephalinase enzyme inhibiting compounds |
| FR2540495B1 (fr) * | 1983-02-07 | 1986-02-14 | Roussel Uclaf | Nouveaux derives de o-mercaptopropanamide et de ses homologues, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
-
1983
- 1983-02-07 FR FR8301863A patent/FR2540498B1/fr not_active Expired
-
1984
- 1984-01-10 ES ES528765A patent/ES528765A0/es active Granted
- 1984-01-25 ZA ZA84571A patent/ZA84571B/xx unknown
- 1984-02-01 DE DE8484400217T patent/DE3460841D1/de not_active Expired
- 1984-02-01 AT AT84400217T patent/ATE22555T1/de not_active IP Right Cessation
- 1984-02-01 EP EP84400217A patent/EP0117183B1/fr not_active Expired
- 1984-02-06 DK DK051484A patent/DK169254B1/da not_active IP Right Cessation
- 1984-02-06 JP JP59018511A patent/JPS59152368A/ja active Granted
- 1984-02-06 PT PT78071A patent/PT78071B/pt not_active IP Right Cessation
- 1984-02-06 AU AU24202/84A patent/AU569487B2/en not_active Ceased
- 1984-02-06 HU HU84481A patent/HU191991B/hu not_active IP Right Cessation
- 1984-02-06 CA CA000446814A patent/CA1215648A/fr not_active Expired
- 1984-02-06 US US06/577,032 patent/US4567198A/en not_active Expired - Fee Related
- 1984-02-06 GR GR73712A patent/GR81411B/el unknown
- 1984-02-07 KR KR1019840000560A patent/KR910008183B1/ko not_active Expired
- 1984-02-07 NZ NZ207057A patent/NZ207057A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8500899A1 (es) | 1984-11-01 |
| ZA84571B (en) | 1985-02-27 |
| PT78071B (fr) | 1986-06-11 |
| AU569487B2 (en) | 1988-02-04 |
| FR2540498B1 (fr) | 1986-02-14 |
| KR850001163A (ko) | 1985-03-16 |
| KR910008183B1 (ko) | 1991-10-10 |
| FR2540498A1 (fr) | 1984-08-10 |
| EP0117183A1 (fr) | 1984-08-29 |
| JPH0455188B2 (enrdf_load_stackoverflow) | 1992-09-02 |
| ATE22555T1 (de) | 1986-10-15 |
| US4567198A (en) | 1986-01-28 |
| CA1215648A (fr) | 1986-12-23 |
| DE3460841D1 (en) | 1986-11-06 |
| DK169254B1 (da) | 1994-09-26 |
| GR81411B (enrdf_load_stackoverflow) | 1984-12-11 |
| ES528765A0 (es) | 1984-11-01 |
| JPS59152368A (ja) | 1984-08-31 |
| DK51484A (da) | 1984-08-08 |
| DK51484D0 (da) | 1984-02-06 |
| AU2420284A (en) | 1984-08-16 |
| PT78071A (fr) | 1984-03-01 |
| EP0117183B1 (fr) | 1986-10-01 |
| HU191991B (en) | 1987-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE840279L (en) | Mercaptoalkanoic acid derivatives | |
| IL92830A (en) | Capsaicin derivatives, their preparation and pharmaceutical compositions containing them | |
| NZ207057A (en) | Substituted amide derivatives and pharmaceutical compositions | |
| FR2664269A1 (fr) | Nouveaux derives n-substitues d'alpha-mercapto alkylamines, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant. | |
| DE69414194T2 (de) | Aminosäurederivate und ihre Verwendung als Enkephalinase-Inhibitoren | |
| CA1330446C (en) | Phenolic thioalkylamides as inhibitors of 5-lipoxygenase | |
| FR2467840A1 (fr) | Acides benzoyl-3 nitro-2 phenylacetiques et sels metalliques, amides et esters correspondants utiles notamment comme medicaments anti-inflammatoires compositions therapeutiques et formes pharmaceutiques les contenant et procedes et intermediaires pour leur preparation | |
| DE69402004T2 (de) | Beta-mercapto-propanamidderivate verwendbar zur Behandlung kardiovaskularer Krankheiten oder Erkrankungen | |
| FR2556721A1 (fr) | Nouveaux derives de o-mercaptopropanamide d'o amino-acides, leur procede de preparation, leur application comme medicaments et les compositions les renfermant | |
| KR880002002B1 (ko) | N-(1,3-디티올란-2-일리덴)아닐린 유도체 및 이의 제조방법 | |
| CA1141380A (fr) | Derives de benzoyl-2-nitro-4 anilides, leur preparation et leur application en tant que medicaments | |
| US4301167A (en) | 2-Amino thiazoline derivatives | |
| EP0813529B1 (fr) | Analogues de l'arginine ayant une activite en tant qu'inhibiteurs de la no synthase | |
| DE68913856T2 (de) | Cycloalkylthiazol-Derivate. | |
| CA1251445A (fr) | PROCEDE DE PREPARATION DE DERIVES DE L'.omega.- MERCAPTOPROPANAMIDE ET DE LEURS SELS | |
| US4839358A (en) | Alpha-mercaptomethyl-benzene propanamides, pharmaceutical compositions and use | |
| US3697590A (en) | Phenylacetic acids and their salts | |
| DE69528984T2 (de) | Hemmung der leukotrienbiosynthese mittels harnstoffderivaten | |
| SK278791B6 (sk) | Izochinolínové deriváty, spôsob ich výroby a farma | |
| JPH01156949A (ja) | ４−オキソ−４−（置換フェニル）ブテン酸アミド | |
| FR2559770A1 (fr) | Nouveaux derives de n-alkyl-o-mercaptopropanamide, leurs procedes de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus | |
| CS209866B2 (cs) | Způsob výroby substituovaných amidů kyseliny skořicové | |
| JPH0812659A (ja) | チアゾール誘導体及びこれを含有する医薬製剤 | |
| FR2688218A1 (fr) | Sels d'ammonium quaternaires de composes aromatiques amines, leur preparation et compositions pharmaceutiques les contenant. |